Certain (meth)acrylic and polyurethane polymers and oligomers containing perfluoroalkyl groups are known to provide water/oil repellency and anti-soil properties to various substrates such as concrete, paper, polymers, and fibers. Usually, these polymers or oligomers are made either by free-radical polymerization of perfluoroalkyl (meth)acrylates or by reaction of oligomeric/polymeric isocyanates with perfluoroalkyl alcohols or amines.
The compositions and molecular weights of perfluoroalkyl (meth)acrylate copolymers are limited due to their different reactivity ratios. Molecular weights of polyurethanes capped with perfluoroalkyl alcohols or amines are limited due to the monofunctionality of the available alcohols/amines. Thus the development of perfluoroalkyl substituted polymers with a wider range of properties than is provided by (meth)acrylic or polyurethane backbones is desirable. Tough and elastomeric polymers based on other monomers with fluorinated side-chains are particularly desirable, but are not provided by the (meth)acrylic or polyurethane systems.
Certain halogenated polymers have been reacted with thiols, e.g., under phase transfer catalysis conditions, to produce a polymer having pendant alkylthio ether side-chains. Perfluoroalkyl terminated neopentyl glycol compounds prepared by substitution of halogenated neopentyl glycol compounds with perfluoroalkyl thiols in the presence of base are described by Falk et al. in U.S. Pat. No. 4,898,981 and U.S. Pat. No. 4,946,992. The resulting compounds are a dimer or trimer of the starting glycol. Polymers having pendant fluoroalkylsulfide groups which retain the original properties of the polymer are desirable. The present invention provides such polymers which retain desirable elastomeric and toughness properties while also providing oil and water repellency and antisoil properties due to the fluoro-containing pendant groups.